Organosilane-containing anionic detergent composition

ABSTRACT

A detergent composition containing an anionic detergent and an organosilane is capable of imparting soil release benefits to hard surfaces washed therewith. Soil adheres to such surfaces less strongly thereby making them easier to clean. The detergent composition can be formulated for use in a wide range of applications, e.g., as a light duty liquid composition, car wash composition, oven cleaner, window cleaner or toilet bowl cleaner.

BACKGROUND OF THE INVENTION

This invention relates to a detergent composition containing an anionicdetergent and an organosilane compound. The detergent compositions ofthis invention are intended for use on hard, i.e., metallic and vitreoussurfaces. More particularly, the inclusion of the hereindescribedorganosilane compound in detergent compositions provides soil releasebenefits to surfaces washed with such compositions.

Detergent compositions intended for use on hard surfaces are continuallybeing reformulated in order to improve their performances. Generally,detergent compositions are formulated to obtain optimum cleaningperformance. Such endeavors have revolved around the use of differentorganic detergents as well as the use of detergent builders and variousadditives, e.g., enzymes, bleaches and pH modifiers. Considerations suchas human safety, compatibility of components, and equipment safety haveplayed a part in dicatating what components are available for improvingexisting detergent compositions.

Other attempts at insuring that hard surfaces are clean have involvedthe application of various surface coatings to such hard surfaces. Forexample, cookware which has been coated with Teflon provides a surfacewhich is easier to clean. Thus, while soil continues to deposit upon thesurface, its removal is easier by virtue of the coating. Unfortunately,such coatings are relatively expensive. Moreover, such a coating onglassware would be objectionable due to its appearance and/or feel.Since this kind of a coating must be applied by the manufacturer of thecookware or glassware, it must be permanent. This generally involves arelatively heavy coating with the consequent drawback in terms of cost,appearance, and/or feel.

It has now been discovered that a very thin layer of a compoundpossessing soil release benefits can be supplied to metallic andvitreous surfaces by a detergent composition. Thus, when the detergentcomposition is used for cleaning or washing a hard surface, a thinsemi-permanent coating of a compound is laid down. The amount of coatingis sufficient to provide a soil release benefit to the surface, while atthe same time, is not visible or expensive.

Commonly assigned copending patent application "Organosilane-ContainingDetergent Composition", Heckert and Watt, U.S. Ser. No. 570,534, filedApr. 22, 1975, discloses the addition of certain positively chargedorgano silanes to a detergent composition containing a nonionic,zwitterionic, or ampholytic detergent or mixtures thereof as the activedetergent. It has been found that certain of these organosilanes areincompatible with anionic detergents. That is, the positively chargedorganosilane reacts with the negatively charged anionic detergent toeffectively reduce the ability of the organosilane to impart soilrelease benefits to a hard surface.

It accordingly is an object of this invention to provide detergentcompositions which are capable of imparting a soil release benefit tosurfaces contacted therewith.

It is another object of this invention to provide detergent compositionscontaining an anionic detergent and an organosilane which is able toprovide soil release benefits to metallic and vitreous surfaces whenapplied thereto from a wash or rinse solution.

As used herein, all percentages and ratios are by weight unlessotherwise indicated.

SUMMARY OF THE INVENTION

A detergent composition capable of imparting soil release benefits tometallic and vitreous surfaces contacted therewith consistingessentially of:

a. an organosilane having the formula ##STR1## or is a siloxane oligomerthereof wherein R₁ is an alkyl group containing 1 to 4 carbon atoms or

     Z(OC.sub.x H.sub.2x).sub.m

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbons, or an acyl group containing 1 to 4 carbonatoms; R₂ is an alkyl group containing 1 to 12 carbon atoms; a is 0 to2; R₃ is hydrogen or an alkyl group containing 1 to 12 carbon atoms; bis 1 to 3; c is 0 or 1; R₄ is an alkyl, aryl or aryl alkyl groupcontaining 1 to 12 carbon atoms, a carboxy-substituted alkyl groupcontaining 1 to 4 carbon atoms,

     (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen; R₅ is an alkyl, aryl or arylalkyl group containing 1 to 12carbon atoms; X is halide; and Y is nitrogen, sulfur, or phosphorus andthe sum of the carbon atoms in R₂, R₃, and R₅ and R₄ when R₄ is alkyl,aryl, arylalkyl or carboxy-substituted alkyl does not exceed 20 carbonatoms; and

b. a water-soluble organic anionic detergent in a weight ratio oforganosilane to detergent of from 1:1 to 1:10,000.

DESCRIPTION OF THE INVENTION

The subject invention relates to all manner of detergent compositions.As examples, may be mentioned the following: light duty liquid detergentcompositions, car wash detergent compositions, window cleaners, ovencleaners and toilet bowl cleaners. The previous listing is merelyillustrative and is in no way limiting. Such compositions are furtherdescribed hereinafter. The compositions may be used on any metallic orvitreous surface where a soil release benefit is desired. Examples ofsuch surfaces are cooking utensils (e.g. metallic pots, pans andskilltes), tableware (e.g. china, glasses, ceramic ware and flatware),oven walls, windows, and porcelain surfaces (e.g. bathtubs, sinks, andtoilet bowls).

The detergent compositions of this invention contain an organosilane anda water-soluble anionic detergent in a ratio of organosilane to anionicdetergent of from 1:1 to 1:10,000, preferably 1:1 to 1:500, mostpreferably 1:3 to 1:60. The organosilane has the following formula:##STR2## or is a siloxane oligomer thereof wherein R₁ is an alkyl groupcontaining 1 to 4 carbon atoms or

     Z(OC.sub.x H.sub.2x).sub.m

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms; R₂ is an alkyl group containing 1 to 12 carbon atoms; a is 0 to2; R₃ is hydrogen or an alkyl group containing 1 to 12 carbon atoms; bis 1 to 3; c is 0 or 1; R₄ is an alkyl, aryl or arylalkyl groupcontaining 1 to 12 carbon atoms, a carboxy-substituted alkyl groupcontaining 1 to 4 carbon atoms,

     (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen; R₅ is an alkyl, aryl or arylalkyl group containing 1 to 12carbon atoms; X is halide; Y is nitrogen, sulfur or phosphorus and thesum of the carbon atoms in R₂, R₃, R₅, and R₄ when R₄ is alkyl, aryl,arylalkyl or carboxy-substituted alkyl does not exceed 20. Preferably Xis chloride or bromide and b is 1 and the sums of R₂, R₃, R₅ and R₄ whenR₄ is alkyl, aryl, arylalkyl or carboxy-alkyl does not exceed 15.

It should be understood that the R₄ in the above formula and theformulae to follow may be the same or different. It should further beunderstood that when Y is S, there will be only one R₄ substituent.Also, when one R₄ is oxygen or, under basic conditions, the anion of acarboxylic acid substituted alkyl, the counter ion X⁻ is not extant. The1 to 4 carbon atoms in the carboxy-substituted alkyl group is inclusiveof the carboxyl group. The aryl and arylalkyl groups of R₄ and R₅contain 6 to 12 carbon atoms.

Classes of organosilane compounds and their preparation which fit theabove description follow. ##STR3## wherein R₁ is a C₁₋₄ alkyl group, bis from 1-3, R₄ is a C₁₋₁₂ alkyl, aryl or arylalkyl group, acarboxy-substituted C₁₋₄ alkyl group,

     (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group or aC₁₋₁₄ acyl group, or oxygen provided only one R₄ is oxygen, R₅ is aC₄₋₁₂ alkyl, aryl or arylalkyl group, X is a halide, Y is N, S or P, andthe sum of the carbon atoms in R₅ and R₄ when R₄ is alkyl, aryl,arylalkyl or carboxy-substituted alkyl does not exceed 20.

When b is 3 and R₄ is a C₁₋₁₂ alkyl, aryl or arylalkyl group, the classof compounds represented by Formula I is prepared by the followingroute: ##STR4##

The trihalosilane (where the halogen is chlorine or bromine) is reactedwith the allyl chloride at about 100° C. for from 4 to 10 hours in thepresence of a catalyst, e.g., chloroplatinic acid or platinum. Theresultant gammahalopropyltrihalosilane is reacted with a lower alcoholto produce the gamma-halopropyltrialkoxysilane. At least threeequivalents of alcohol per equivalent of halopropyltrihalosilane areadded slowly to the silane. The gamma-halopropyltrihalosilane may bedissolved in an inert solvent, preferably hexane or pentane. (See W.Noll, "Chemistry and Technology of Silanes", Academic Press, New York,1968, page 81 for the alcoholysis of halosilanes.) One equivalent of thegamma-halopropyltrialkoxysilane is reacted with one equivalent of thetertiary amine, tertiary phosphine, or dialkylsulfide to produce theorganosilane. An inert solvent, preferably of high dielectric constant,may be used. The reaction is carried out at temperatures of from 40° to120° C. and a time of 2 to 10 hours for the reaction of thebromopropyltrialkoxysilane and 120° to 150° C. for 2 to 20 hours for thereaction of the chloropropyltrialkoxysilane.

The compounds of Formula I when at least one R₄ is a carboxy-substitutedC₁₋₄ alkyl group are prepared in the same manner except for the lastreaction step. Here, a tertiary amine, tertiary phosphine ordialkylsulfide having a carboxy-containing alkyl group(s) is reactedwith the alpha, beta or gamma-haloalkyltrialkoxysilane at 50° to 200° C.for 2 hours to 20 hours. Such carboxy-substituted tertiary amines,tertiary phosphines, and dialkylsulfides are produced by reacting

     R.sub.4 YHR.sub.5 or HYR.sub.5

(where Y is sulfur)

with

     X(CH.sub.2).sub.1-4 COOH

in the presence of base at elevated temperatures, e.g. 50° to 150° C.

The compounds of Formula I when at least one R₄ is

     (C.sub.x H.sub.2x O).sub.m Z

with x, m and Z as defined above are produced in the manner given aboveexcept for the last reaction step. Thus, alphabeta- andgamma-haloalkyltrialkoxysilane is reacted with a tertiary amine,tertiary phosphine, or dialkylsulfide where at least one substituent is

     (C.sub.x H.sub.2x O).sub.m Z

the reaction takes place at a temperature of 50° to 200° C. and a timeof from 2 to 10 hours.

Compounds of Formula I when one R₄ is oxygen are prepared by followingthe reactions outlined above up to the last reaction step. At thispoint, a dialkyl amine, dialkyl phosphine or alkylthiol is reacted withthe halosilane at 50° to 200° C. for from 4 to 10 hours and then withbase to produce an intermediate tertiary amine, phosphine, or dialkylsulfide. These intermediates are then reacted with H₂ O₂ at 20° to 100°C. or preferably O₃ in an inert solvent at -80° to 20° C. to yield theorganosilane.

When b is 2 in Formula I, a trihalovinylsilane of formula

     X.sub.3 SiCH=CH.sub.2

(which is commercially available) is reacted with hydrogen bromide inthe presence of peroxide or light to produce abeta-haloethyltrihalosilane. This compound is reacted with an alcoholand thereafter with an appropriate amine, phosphine, or sulfide in themanner discussed above for the preparation of the compounds of Formula Iwhen b is 3.

When b is 1 in Formula I, the starting reactant is a commerciallyavailable trihalomethylsilane of formula

     X.sub.3 SiCH.sub.3.

this silane is reacted with chlorine or, preferably a half mole ofbromine and a half mole of chlorine in the presence of light (such asprovided by an ordinary tungsten or fluorescent lamp). The resultantalpha-halomethyltrihalosilane is reacted with an alcohol and thereafteran appropriate amine, phosphine or sulfide in the manner discussed abovewith the compounds of Formula I when b is 3.

Examples of compunds illustrative of compounds of Formula I follow:

    (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25 Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.6 H.sub.5  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(C.sub.2 H.sub.5).sub.2 C.sub.10 H.sub.21  Br.sup.-

    (C.sub.3 H.sub.7 O).sub.3 SiCH.sub.2 N.sup.+(C.sub.3 H.sub.7).sub.2 C.sub.6 H.sub.4 CH.sub.3  Br.sup.-

    (C.sub.4 H.sub.9 O).sub.3 Si(CH.sub.2).sub.2 N.sup.+(C.sub.2 H.sub.5) (CH.sub.2 C.sub.6 H.sub.5).sub.2  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 P.sup.+(C.sub.2 H.sub.5).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 P.sup.+(C.sub.4 H.sub.9).sub.2 C.sub.6 H.sub.5  Cl.sup.-

    (C.sub.3 H.sub.7 O).sub.3 Si(CH.sub.2).sub.2 S.sup.+(CH.sub.3)C.sub.6 H.sub.5  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 CH.sub.2 S.sup.+(C.sub.2 H.sub.5)C.sub.8 H.sub.17  Br.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.4 COOH).sub.2 C.sub.10 H.sub.21  Br.sup.-

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.2 COOH) (CH.sub.3)C.sub.12 H.sub.25  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.2 P.sup.+(C.sub.3 H.sub.6 COOH) (C.sub.2 H.sub.5)C.sub.10 H.sub.21  Cl.sup.-

    (C.sub.4 H.sub.9 O).sub.3 SiCH.sub.2 S.sup.+(C.sub.3 H.sub.6 COOH)C.sub.6 H.sub.13  Br.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.4 OH).sub.2 C.sub.8 H.sub.17  Cl.sup.-

    (C.sub.4 H.sub.9 O).sub.3 Si(CH.sub.2).sub.3 P.sup.+(C.sub.4 H.sub.8 OH).sub.2 C.sub.6 H.sub.4 CH.sub.3  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 S.sup.+(C.sub.3 H.sub.6 OH)C.sub.10 H.sub.21  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+(O).sup.-(CH.sub.3)C.sub.12 H.sub.25

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 P.sup.+(O).sup.-(C.sub.2 H.sub.5)C.sub.12 H.sub.25

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.2 S.sup.+(O).sup.-C.sub.10 H.sub.21

    (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.3 H](CH.sub.3)C.sub.8 H.sub.17  Cl.sup.-

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.2 N.sup.+[(C.sub.4 H.sub.8 O).sub.15 CH.sub.3 ](CH.sub.3)C.sub.6 H.sub.13

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+[(C.sub.2 H.sub.4 O).sub.6 H].sub.2 C.sub.10 H.sub.21  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.3 COCH.sub.3 ].sub.2 C.sub.8 H.sub.17  Cl.sup.-

    (C.sub.3 H.sub.7 O).sub.3 SiCH.sub.2 P.sup.+[(C.sub.3 H.sub.6 O).sub.12 H].sub.2 CH.sub.2 C.sub.6 H.sub.5  Cl.sup.-

    (C.sub.4 H.sub.9 O).sub.3 Si(CH.sub.2).sub.3 P.sup.+[(C.sub.2 H.sub.4 O).sub.4 C.sub.3 H.sub.7 ](CH.sub.3).sub.2  Br.sup.-

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.2 P.sup.+[(C.sub.2 H.sub.4 O).sub.5 COC.sub.2 H.sub.5 ].sub.2 C.sub.4 H.sub.9  Br.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.5 H]C.sub.10 H.sub.21  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.2 S.sup.+[(C.sub.3 H.sub.6 O).sub.8 C.sub.3 H.sub.7 ]CH.sub.3  Br.sup.-

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 S.sup.+[(C.sub.2 H.sub.4 O).sub.12 COC.sub.4 H.sub.9 ]CH.sub.3  Cl.sup.- ##STR5## where R.sub.1 is a C.sub.1-14 alkyl group, R.sub.2 is a C.sub.1-12 alkyl group a is 1 or 2, b is 1-3, R.sub.4 is a C.sub.1-12 alkyl, aryl or arylalkyl group, a carboxy-substituted C.sub.1-4 alkyl group,

     (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group or aC₁₋₄ acyl group, or oxygen provided only one R₄ is oxygen, R₅ is a C₁₋₁₂alkyl, aryl or arylalkyl group, X is halide, Y is N, S or P, and the sumof the carbon atoms in R₂, R₅ and R₄ when R₄ is alkyl, aryl, arylalkylor carboxy-substituted alkyl, does not exceed 20.

The compounds of Formula II are prepared in a manner similar to thepreparation of the compounds of Formula I except for the fact that thestarting reactants (when b is 1, 2, or 3) all have a c₁₋₁₂ alkyl groupor two C₁₋₁₂ alkyl groups attached to the Si atom in place of a halogenatom(s). The starting reactant is commercially available when R₂ is CH₃.When R₂ is C₂ H₅ or greater, the compound is prepared by reacting asilane with an appropriate olefin. Thus,

     X.sub.3.sub.-a SiH.sub.1.sub.+a

is reacted with a C₂ to C₁₂ olefin to obtain the desired startingreactant. The remaining reaction steps and conditions for producing thedesired organosilane of Formula II are essentially the same as forproducing the compounds of Formula I.

Examples of compounds of Formula II are:

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.2 C.sub.6 H.sub.13 Si(CH.sub.2).sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.4 H.sub.9  Cl.sup.-

    (C.sub.3 H.sub.7 O) (C.sub.3 H.sub.7).sub.2 Si(CH.sub.2).sub.3 N.sup.+(C.sub.2 H.sub.5).sub.2 C.sub.8 H.sub.17  Cl.sup.-

    (CH.sub.3 O) (CH.sub.3).sub.2 SiCH.sub.2 P.sup.+(CH.sub.3).sub.2 C.sub.10 H.sub.21  Cl.sup.-

    (C.sub.3 H.sub.7 O).sub.2 C.sub.2 H.sub.5 Si(CH.sub.2).sub.2 S.sup.+(C.sub.4 H.sub.9)C.sub.6 H.sub.12 C.sub.6 H.sub.5  Cl.sup.-

    (CH.sub.3 O).sub.2 C.sub.8 H.sub.17 Si(CH.sub.2).sub.3 N.sup.+(C.sub.2 H.sub.4 COOH) (CH.sub.3)C.sub.4 H.sub.9  Cl.sup.-

    (C.sub.2 H.sub.5 O) (CH.sub.3).sub.2 Si(CH.sub.2).sub.2 P.sup.+(CH.sub.2 COOH).sub.2 C.sub.10 H.sub.21  Cl.sup.-

    (C.sub.3 H.sub.7 O).sub.2 CH.sub.3 SiCH.sub.2 S.sup.+(C.sub.3 H.sub.9 COOH)C.sub.6 H.sub.13  Cl.sup.-

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.4 OH).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    (C.sub.3 H.sub.7 O) (CH.sub.3).sub.2 SiCH.sub.2 P.sup.+(C.sub.3 H.sub.6 OH) (C.sub.4 H.sub.9).sub.2  Br.sup.-

    (C.sub.4 H.sub.9 O).sub.2 CH.sub.3 Si(CH.sub.2).sub.3 S.sup.+(C.sub.3 H.sub.6 OH)CH.sub.3  Br.sup.-

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH.sub.2 N.sup.+(O).sup.-(CH.sub.3)C.sub.10 H.sub.21

    (CH.sub.3 O).sub.2 C.sub.10 H.sub.21 Si(CH.sub.2).sub.2 P.sup.+(O).sup.-(C.sub.4 H.sub.9).sub.2

    (C.sub.4 H.sub.9 O) (CH.sub.3).sub.2 Si(CH.sub.2).sub.3 S.sup.+(O).sup.-C.sub.8 H.sub.17

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH.sub.2 N.sup.+[(C.sub.3 H.sub.6 O).sub.20 H].sub.2 C.sub.6 H.sub.5  Cl.sup.-

    (CH.sub.3 O).sub.2 C.sub.2 H.sub.5 Si(CH.sub.2).sub.2 N.sup.+[(C.sub.4 H.sub.8 O).sub.6 C.sub.2 H.sub.5 ].sub.2 CH.sub.3  Cl.sup.-

    (C.sub.2 H.sub.5 O) (CH.sub.3).sub.2 SiCH.sub.2 P.sup.+[(C.sub.2 H.sub.4 O).sub.2 H](C.sub.6 H.sub.5).sub.2  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.2 C.sub.8 H.sub.17 Si(CH.sub.2).sub.3 P.sup.+[(C.sub.2 H.sub.4 O).sub.4 C.sub.3 H.sub.7 ].sub.2 C.sub.4 H.sub.9 Cl.sup.+

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH.sub.2 P.sup.+[(C.sub.2 H.sub.4 O).sub.6 COCH.sub.3 ].sub.2 C.sub.8 H.sub.17  Cl.sup.-

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH.sub.2 S.sup.+[(C.sub.3 H.sub.6 O).sub.2 H]C.sub.6 H.sub.13  Cl.sup.-

    (C.sub.2 H.sub.5 O)(C.sub. 2 H.sub.5).sub.2 Si(CH.sub.2).sub.3 S.sup.+[(C.sub.2 H.sub.4 O).sub.5 CH.sub.3 ]C.sub.8 H.sub.17  Br.sup.-

    (C.sub.2 H.sub.5 O).sub.2 C.sub.10 H.sub.21 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.2 COC.sub.2 H.sub.5 ](C.sub.4 H.sub.9).sub.2  Cl.sup.-

    (CH.sub.3 O).sub.2 C.sub.4 H.sub.9 Si(CH.sub.2).sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.2 COCH.sub.3 ]C.sub.12 H.sub.25  Br.sup.-

Compounds of Formulas I and II when R₄ is an alkyl, aryl, arylalkylgroup or oxygen and disclosed in British Patents Nos. 686,068 and882,053 and U.S. Pats. Nos. 2,955,127, 3,557,178, 3,730,701 and3,817,739. Compounds of Formulas I and II when R₄ is acarboxy-substituted alkyl group or (C_(x) H_(2x) O)_(m) Z are disclosedin commonly assigned copending patent application "OrganosilaneCompounds" by Heckert and Watt, U.S. Ser. No. 570,532, filed Apr. 22,1975. (The disclosure of this application is herein incorporated byreference.) ##STR6## wherein R₁ is a C₁₋₄ alkyl group, a is 0 to 2, R₂is a C₁₋₁₂ alkyl group, R₃ is a C₁₋₁₂ alkyl group, R₄ is a C₁₋₁₂ alkyl,aryl or arylalkyl group, a carboxy-substituted C₁₋₄ alkyl group,

     (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group or aC₁₋₄ acyl group, or oxygen provided only one R₄ is oxygen, R₅ is a C₁₋₁₂alkyl, aryl or arylalkyl group, X is halide, Y is N, S or P and the sumof the carbon atoms in R₂, R₃, R₅ and R₄ when R₄ is alkyl, aryl,arylalkyl or carboxy-substituted alkyl does not exceed 20.

The compounds of Formula III when a is 0 and R₄ is an alkyl group areprepared by the following route: ##STR7##

The trihalosilane is reacted with an olefin at 100° C. for 4 to 10 hoursunder a pressure of 50 to 300 psi. in the presence of a chloroplatinicacid or platinum catalyst to produce the trihaloalkylsilane. Thisreaction is reported by F. P. Mackay, O. W. Steward and P. G. Campbellin "Journal of the American Chemical Society", 79, 2764 (1957) and J. L.Speier, J. A. Webster and S. W. Barnes in Journal of the AmericanChemical Society, 79, 974 (1957). The trihaloalkylsilane is thenhalogenated in a known manner by treating it with halogen in thepresence of light (such as that provided by ordinary tungsten offluorescent lamps). Preferably, halogenation is carried out to onlypartial completion and a distillation is performed to recycle unreactedalkylsilane. The remaining reactions are the same as those describedabove in connection with the preparation of the compounds of Formula I.

When a is 1 or 2, the preparation of the compounds is essentially thesame except for the use of an alkyl substituted silane as the startingreactant.

When R₄ is a carboxy-substituted C₁₋₄ alkyl group, oxygen or

     (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group, or aC₁₋₄ acyl group, an appropriate amine, phosphine, or sulfide is used inthe reaction step as discussed above for the preparation of similarlysubstituted compounds of Formula I.

The compounds that follow are illustrative of compounds of Formula III.

    (C.sub.2 H.sub.5 O).sub.3 SiCH(C.sub.8 H.sub.17)N.sup.+(CH.sub.3).sub.2 C.sub.8 H.sub.17  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH(C.sub.10 H.sub.21)N.sup.+(C.sub.2 H.sub.4 COOH).sub.2 CH.sub.3  Cl.sup.-

    (C.sub.3 H.sub.7 O).sub.2 CH.sub.3 SiCH(C.sub.12 H.sub.25)N.sup.+(C.sub.2 H.sub.4 OH)(CH.sub. 3).sub.2  Cl.sup.-

    (C.sub.4 H.sub.9 O).sub.3 SiCH(C.sub.3 H.sub.7)N.sup.+[(C.sub.2 H.sub.4 O).sub.10 H].sub.2 C.sub.6 H.sub.13  Br.sup.-

    (CH.sub.3 O).sub.3 SiCH(C.sub.10 H.sub.21)N.sup.+[(C.sub.2 H.sub.4 O).sub.2 C.sub.3 H.sub.7 ](CH.sub.3)C.sub.6 H.sub.5  Br.sup.-

    (CH.sub.3 O).sub.3 SiCH(CH.sub.3)N.sup.+[(C.sub.2 H.sub.4 O).sub.3 COC.sub.2 H.sub.5 ](C.sub.2 H.sub.5).sub.2  Br.sup.-

    (C.sub.2 H.sub.5 O).sub.2 CH.sub.3 SiCH(C.sub.8 H.sub.17)N.sup.+(O).sup.-(CH.sub.3).sub.2

    (CH.sub.3 O).sub.3 SiCH(C.sub.8 H.sub.17)P.sup.+(CH.sub.3).sub.3  Cl.sup.-

    (CH.sub.3 O).sub.2 CH.sub.3 SiCH(CH.sub.3)P.sup.+(C.sub.3 H.sub.6 COOH).sub.2 C.sub.2 H.sub.4 C.sub.6 H.sub.5  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH(C.sub.10 H.sub.21)P.sup.+(C.sub.2 H.sub.4 OH)C.sub.4 H.sub.9  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH(C.sub.3 H.sub.7)P.sup.+ (O).sup.-(CH.sub.3)C.sub.12 H.sub.25

    (CH.sub.3 O).sub.3 SiCH(C.sub.8 H.sub.17)P.sup.+[(C.sub.2 H.sub.4 O).sub.6 H].sub.2 CH.sub.3  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH(C.sub.6 H.sub.13)P.sup.+[C.sub.3 H.sub.6 O).sub.2 C.sub.2 H.sub.5 ](CH.sub.3).sub.2  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH(CH.sub.3)S.sup.+(CH.sub.3)C.sub.10 H.sub.21 Br.sup.-

    (C.sub.2 H.sub.5 O).sub.2 CH.sub.3 SiCH(C.sub.12 H.sub.25)S.sup.+(C.sub.3 H.sub.6 COOH)CH.sub.3  Cl.sup.-

    (CH.sub.3 O).sub.2 C.sub.12 H.sub.25 SiCH(C.sub.2 H.sub.5)S.sup.+(C.sub.2 H.sub.4 OH)C.sub.2 H.sub.5  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH(C.sub.10 H.sub.21)S.sup.+(O).sup.-C.sub.5 H.sub.11

    (C.sub.2 H.sub.5 O).sub.3 SiCH(C.sub.4 H.sub.9)S.sup.+[(C.sub.3 H.sub.6 O).sub.10 H]C.sub.6 H.sub.5  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH(CH.sub.3)S.sup.+[(C.sub.2 H.sub.4 O).sub.20 C.sub.2 H.sub.5 ]CH.sub.3  Br.sup.-

Commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt, U.S. Ser. No. 570,537, filed Apr. 22, 1975discloses the preparation of these compounds. (The disclosure of thisapplication is herein incorporated by reference). ##STR8## wherein Z ishydrogen, a C₁₋₃ alkyl group or a C₁₋₄ acyl group, x is 2-4, m is 1-20,a is 0-2, R₂ is a C₁₋₁₂ alkyl group, b is 1-3, R₄ is a C₁₋₁₂ alkyl, arylor arylalkyl group, a carboxy-substituted C₁₋₄ alkyl group

     (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen, R₅ is a C₁₋₁₂ alkyl, aryl or arylalkyl group, X is halide, Y isN, S or P and the sum of the carbon atoms in R₂, R₅ and R₄ when R₄ isalkyl, aryl, arylalkyl or carboxy-substituted alkyl does not exceed 20.

The compounds with Formula IV are prepared in substantially the samemanner as those of Formula II with the exception that the R₁ OH used inthe alcoholysis step is

     Z(OC.sub.x H.sub.2x).sub.m OH

or alternatively the compounds of Formula II are heated in the presenceof

     Z(OC.sub.x H.sub.2x).sub.m OH

under conditions such that R₁ OH is removed from the system.

Exemplary compounds of Formula IV are as follows:

    [CH.sub.3 (OC.sub.2 H.sub.4)O].sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    [CH.sub.3 (OC.sub.2 H.sub.4).sub.5 O].sub.2 CH.sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.2 COOH).sub.2 C.sub.10 H.sub.21  Cl.sup.-

    [H(OC.sub.3 H.sub.6).sub.3 O].sub.3 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.4 OH)(CH.sub. 3)(C.sub.12 H.sub.25)  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.18 O].sub.3 Si(CH.sub.2).sub.2 N.sup.+(O).sup.-(CH.sub.3)C.sub.10 H.sub.21

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.10 O].sub.3 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.14 H].sub.2 C.sub.6 H.sub.12 C.sub.6 H.sub.5  Cl.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4).sub.8 O].sub.2 C.sub.6 H.sub.13 SiCH.sub.2 N.sup.+[(C.sub.3 H.sub.6 O)CH.sub.3 ](CH.sub.3).sub.2  Br.sup.-

    [H(OC.sub.4 H.sub.8).sub.8 O].sub.3 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.4 COCH.sub.3 ].sub.2 CH.sub.3  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.2 O].sub.3 Si(CH.sub.2).sub.2 P.sup.+(CH.sub.3).sub.2 C.sub.10 H.sub.21  Br.sup.-

    [CH.sub.3 (OC.sub.3 H.sub.6).sub.14 O].sub.3 SiCH.sub.2 P.sup.+(C.sub.2 H.sub.4 COOH)(C.sub. 6 H.sub.13).sub.2  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4)O].sub.2 CH.sub.3 Si(CH.sub.2).sub.2 P.sup.+(C.sub.4 H.sub.8 OH)(CH.sub. 3)C.sub.6 H.sub.5  Cl.sup.-

    [CH.sub.3 (OC.sub.2 H.sub.4).sub.8 O].sub.3 SiCH.sub.2 P.sup.+(O).sup.-(CH.sub.3)C.sub.8 H.sub.17

    [C.sub.2 H.sub.5 OC(OC.sub.2 H.sub.4).sub.2 O].sub.3 Si(CH.sub.2).sub.3 P.sup.+[C.sub.2 H.sub.4 O).sub.8 H].sub.2 C.sub.6 H.sub.13  Cl.sup.-

    [CH.sub.3 (OC.sub.4 H.sub.8)O].sub.3 SiCH.sub.2 P.sup.+[(C.sub.3 H.sub.6 O).sub.2 C.sub.3 H.sub.7 ](C.sub.4 H.sub.9).sub.2  Br.sup.-

    [C.sub.2 H.sub.5 OC(OC.sub.2 H.sub.4)O].sub.3 SiCH.sub.2 S.sup.+(CH.sub.3)C.sub.8 H.sub.17  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.4 O].sub.3 Si(CH.sub.2).sub.2 S.sup.+(C.sub.2 H.sub.4 COOH)C.sub.12 H.sub.25  Br.sup.-

    [CH.sub.3 (OC.sub.2 H.sub.4).sub.20 O].sub.3 Si(CH.sub.2).sub.3 S.sup.+(C.sub.3 H.sub.6 OH)C.sub.12 H.sub.25  Br.sup.-

    [H(OC.sub.3 H.sub.6).sub.12 O].sub.3 Si(CH.sub.2).sub.2 S.sup.+(O).sup.-C.sub.5 H.sub.11

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.4 O].sub.3 SiCH.sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.20 H]CH.sub.3  Br.sup.-

    [H(OC.sub.2 H.sub.4).sub.12 O].sub.3 Si(CH.sub.2).sub.3 S.sup.+[(C.sub.2 H.sub.4 O)C.sub.3 H.sub.7 ]C.sub.6 H.sub.4 CH.sub.3  Cl.sup.-

Commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt U.S. Ser. No. 570,539, filed Apr. 22, 1975 disclosesthe preparation of these compounds. (The disclosure of this applicationis herein incorporated by reference.) ##STR9## wherein Z is hydrogen, aC₁₋₃ alkyl group or a C₁₋₄ acyl group, x is 2- 4, m is 1- 20, R₂ is aC₁₋₁₂ alkyl group, R₁ is a C₁₋₄ alkyl group, a is 0 or 1, d is 1 or 2provided a+d does not exceed 2, b is 1-3, R₄ is a C.sub. 1-12 alkyl,aryl or arylalkyl group, a carboxy-substituted C₁₋₄ alkyl group,

     (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are defined above, or oxygen provided only one R₄ isoxygen, R₅ is a C₁₋₁₂ alkyl, aryl or aryl alkyl group, X is halide, Y isN, S or P and the sum of the carbon atoms in R₂, R₅ and R₄ when R₄ isalkyl, aryl, arylalkyl or carboxy-substituted alkyl does not exceed 20.

The compounds of Formula V are formed in substantially the same manneras those of Formula II except that a mixture of R₁ OH and

     Z(OC.sub.x H.sub.2x).sub.m OH

in the desired ratio is used in place of R₁ OH or, alternatively, thecompounds of Formula II are heated with less than 3-a equivalents of

     Z(OC.sub.x H.sub.2x).sub.m OH

under conditions such that R₁ OH is removed from the system.

Examples of illustrative compounds follow:

    [H(OC.sub.2 H.sub.4).sub.5 O](CH.sub.3)(C.sub. 2 H.sub.5 O)SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4).sub.3 O](CH.sub.3 O).sub.2 Si(CH.sub.2).sub.3 N.sup.+(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 Cl.sup.-

    [H(OC.sub.4 H.sub.8).sub.6 O](C.sub.2 H.sub.5).sub. 2 Si(CH.sub.2).sub.3 N.sup.+[(C.sub.2 H.sub.4 O).sub.10 H].sub.2 C.sub.12 H.sub.25  Br.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.3 O].sub.2 (C.sub.2 H.sub.5 O)Si(CH.sub.2).sub.2 N.sup.+](C.sub.2 H.sub.4 O)C.sub.2 H.sub.5 ].sub.2 (C.sub.6 H.sub.5 CH.sub.3)  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.12 O](C.sub.4 H.sub.8 O).sub.2 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.4 COCH.sub.3 ].sub.2 C.sub.10 H.sub.21 Cl.sup.-

    [C.sub. 2 H.sub. 5 (OC.sub.2 H.sub.4).sub.3 O](C.sub.2 H.sub.5)(CH.sub. 3 O)SiCH.sub.2 N.sup.+(O).sup.-(CH.sub.3)C.sub.6 H.sub.13

    [H(OC.sub.3 H.sub.6).sub.12 O](C.sub.2 H.sub.5 O).sub.2 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.5 COOH) (CH.sub.3)C.sub.10 H.sub.21  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.14 O].sub.2 (C.sub.4 H.sub.9 O)Si(CH.sub.2).sub.3 N.sup.+(C.sub.4 H.sub.8 OH)(CH.sub. 3)C.sub.7 H.sub.15  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.16 O].sub.2 (CH.sub.3 O)SiCH.sub.2 P.sup.+(CH.sub.3).sub.2 C.sub.6 H.sub.4 C.sub.2 H.sub.5  Cl.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4).sub.6 O](C.sub.2 H.sub.5)(CH.sub. 3 O)SiCH.sub.2 P.sup.+[(C.sub.2 H.sub.4 O).sub.8 H].sub.2 C.sub.8 H.sub.17 Br.sup.-

    [CH.sub.3 OC(OC.sub.2 H.sub.4).sub.2 O].sub.2 (CH.sub.3 O)Si(CH.sub.2).sub.2 P.sup.+[(C.sub.3 H.sub.6 O).sub.3 C.sub.2 H.sub.5 ](C.sub.4 H.sub.9).sub.2  Cl.sup.-

    [H(OC.sub.4 H.sub.8).sub.2 O](C.sub.12 H.sub.25)(CH.sub. 3 O)SiCH.sub.2 P.sup.+(O).sup.-(CH.sub.3)C.sub.6 H.sub.5

    [C.sub. 2 H.sub. 5 (OC.sub.2 H.sub.4).sub.6 O](CH.sub.3 O).sub.2 SiCH.sub.2 P.sup.+(C.sub.3 H.sub.6 COOH).sub.2 CH.sub.3  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.8 O].sub.2 (C.sub.4 H.sub.9 O)SiCH.sub.2 P.sup.+(C.sub.3 H.sub.6 OH).sub.2 C.sub.2 H.sub.5  Br.sup.-

    [H(OC.sub.2 H.sub.4).sub.10 O].sub.2 (C.sub.3 H.sub.7 O)SiCH.sub.2 S.sup.+ICH.sub.3)C.sub.6 H.sub.12 C.sub.6 H.sub.5  Cl.sup.-

    [H(OC.sub.4 H.sub.8).sub.2 O].sub.2 (CH.sub.3 O)Si(CH.sub.2).sub.3 S.sup.+[(C.sub.2 H.sub.4 O).sub.4 H]CH.sub.3  Br.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4).sub.6 O](CH.sub.3) (CH.sub.3 O)SiCH.sub.2 S.sup.+[(C.sub.3 H.sub.6 O).sub.8 CH.sub.3 ]C.sub.3 H.sub.7 Cl.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.3 O](C.sub.2 H.sub.5 O).sub.2 Si(CH.sub.2).sub.2 S.sup.+(C.sub.2 H.sub.4 OH)C.sub.12 H.sub.25  Cl.sup.-

    [CH.sub.3 (OC.sub.3 H.sub.6).sub.12 O](CH.sub.3 O).sub.2 SiCH.sub.2 S.sup.+(C.sub.3 H.sub.6 COOH)CH.sub.2 C.sub.6 H.sub.5  Br.sup.-

    [H(C.sub.2 H.sub.4 O).sub.6 O](C.sub.12 H.sub.25)(CH.sub.3 O)SiCH.sub.2 S.sup.+(O).sup.-C.sub.6 H.sub.13

commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt U.S. Ser. No. 570,539, filed Apr. 22, 1975 disclosesthe preparation of these compounds. (The disclosure of this applicationis herein incorporated by reference.) ##STR10## wherein Z is hydrogen, aC₁₋₃ alkyl group or a C₁₋₄ acyl group, x is 2-4, m is 1-20, a is 0-2, R₂is a C₁₋₁₂ alkyl group, R₃ is a C₁₋₁₂ alkyl group, R₄ is a C₁₋₁₂ alkyl,aryl or arylalkyl group, a carboxy-substituted C₁₋₄ alkyl group,

     (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group or aC₁₋₄ acyl group, or oxygen provided only one R₄ is oxygen, R₅ is a C₁₋₁₂alkyl, aryl or arylalkyl group, X is halide, Y is N, S or P and the sumof the carbon atoms in R₂, R₃, R₅ and R₄ when R₄ is alkyl, aryl,arylalkyl or carboxy-substituted alkyl does not exceed 20.

The compounds of Formula VI are formed in the same manner as those ofFormula III with the exception that

     Z(OC.sub.x H.sub.2x).sub.m OH

is used in place of

    R.sub.1 OH

during the alcoholysis of the halo-silane. Alternatively, preparationmay be effected by the heating of compounds of Formula III with

    Z(OC.sub.x H.sub.2x).sub.m OH

under conditions such that all of the

    R.sub.1 OH

is removed from the system.

The following compounds illustrate the compounds of Formula VI.

    [CH.sub.3 (OC.sub.2 H.sub.4).sub.3 O].sub.3 SiCH(CH.sub.3)N.sup.+(CH.sub.3).sub.2 C.sub.8 H.sub.17  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4)O].sub.2 CH.sub.3 SiCH(C.sub.2 H.sub.5)N.sup.+ (C.sub.2 H.sub.5)N.sup.- (C.sub.2 H.sub.4 OH).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    [ H(OC.sub.4 H.sub.8).sub.8 O].sub.3 SiCH(C.sub.4 H.sub.9)N.sup.+(C.sub.2 H.sub.4 COOH) (C.sub.4 H.sub.9)CH.sub.2 C.sub.6 H.sub.5  Cl.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.2 O].sub.3 SiCH(C.sub.2 H.sub.5)N.sup.-(O).sup.-(CH.sub.3)C.sub.10 H.sub.21

    [ H(OC.sub.3 H.sub.6).sub.6 O].sub.3 SiCH(C.sub.12 H.sub.25)N.sup.+[(C.sub.2 H.sub.4 O).sub.10 H].sub.2 CH.sub.3  Br.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4)O].sub.3 SiCH(C.sub.3 H.sub.7)N.sup.+[(C.sub.4 H.sub.8 O).sub.3 C.sub.3 H.sub.7 ](C.sub.2 H.sub.5).sub.2  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub. 4 O].sub.3 SiCH(C.sub.2 H.sub.5)N.sup.+[(C.sub.2 H.sub.4 O) .sub.6 COCH.sub.3 ].sub.2 CH.sub.3 Cl.sup.-

    [H(OC.sub.2 H.sub.4) .sub.16 O].sub.3 SiCH(C.sub.4 H.sub.9 )P.sup.+ (C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.4 C.sub.4 H.sub.9  Cl.sup.-

    [CH.sub.3 (OC.sub.2 H.sub.4).sub.16 O].sub.2 C.sub.4 H.sub.9 SiCH(CH.sub.3)P.sup.+(C.sub.3 H.sub.6 COOH).sub.2 C.sub.5 H.sub.11 Cl.sup.-

    [C.sub.2 H.sub.5 OC(OC.sub.2 H.sub.4).sub.5 O].sub.3 SiCH(CH.sub.3)P.sup.+(C.sub.2 H.sub.4 OH) (CH.sub.3)C.sub.12 H.sub.25 Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.2 O].sub.3 SiCH(C.sub.10 H.sub.25)P.sup.+(O).sup.-(CH.sub.3)C.sub.6 H.sub.13

    [H(OC.sub.2 H.sub.4).sub.2 O].sub.3 SiCH(C.sub.8 H.sub.17)P.sup.+[(C.sub.2 H.sub.4 O).sub.6 H].sub.2 C.sub.4 H.sub.9  Br.sup.-

    [CH.sub.3 (OC.sub.4 H.sub.8).sub.2 O].sub.3 SiCH(CH.sub.3)P.sup.+[(C.sub.2 H.sub.4 O)C.sub.2 H.sub.5 ](CH.sub.3).sub.2  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.2 O].sub.3 SiCH(C.sub.6 H.sub.13)S.sup.+(CH.sub.3)C.sub.10 H.sub.21  Cl.sup.-

    [H(OC.sub.2 H.sub.4) .sub.14 O].sub.2 CH.sub.3 SiCH(C.sub.8 H.sub.17)S.sup.+(C.sub.2 H.sub.4 COOH)C.sub.6 H.sub.13  Cl.sup.-

    [H(OC.sub.3 H.sub.6) .sub.4 O].sub.3 SiCH(C.sub.12 H.sub.25)S.sup.+(C.sub.4 H.sub.8 OH)C.sub.6 H.sub.5  Cl.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.3 O].sub.3 SiCH(C.sub.2 H.sub.5)S.sup.+(O).sup.-C.sub.12 H.sub.25

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4)O]SiCH(C.sub.3 H.sub.7)S.sup.+[(C.sub.3 H.sub.6 O)H]C.sub.6 H.sub.13  Cl.sup.-

    [H(OC.sub.4 H.sub.8).sub.4 O].sub.2 CH.sub.3 SiCH(C.sub.4 H.sub.9)S.sup.+]C.sub.2 H.sub.4 O).sub.8 C.sub.3 H.sub.7 ]CH.sub.3 Br.sup.-

Commonly assigned copending patent application "Organosilanee Compounds"by Heckert and Watt U.S. Ser. No. 570,539, filed Apr. 22, 1975 disclosesthe preparation of these compounds. (The disclosure of this applicationis herein incorporated by reference.) ##STR11## wherein Z is hydrogen, aC₁₋₃ alkyl group or a C₁₋₄ acyl group, X is 2-4, m is 1-20, R₂ is aC₁₋₁₂ alkyl group, R₁ is a C₁₋₄ alkyl group, a is 0 or 1, d is 1 or 2provided a+d does not exceed 2, R₃ is a C₁₋₁₂ alkyl group, R₄ is a C₁₋₁₂alkyl, aryl or arylalkyl group, a carboxy-substituted C₁₋₄ alkyl group,(C_(x) H_(2x) O)_(m) Z where x, m and Z are as defined above, or oxygenprovided only one R₄ is oxygen, R₅ is a C₁₋₁₂ alkyl, aryl or arylalkylgroup, X is halide, Y is N, S or P and the sum of the carbon atoms inR₂, R₃, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed 20.

Compounds having Formula VII are prepared in substantially the samemanner as those of Formula III except that a mixture of

    R.sub.1 OH

and

    Z(OC.sub.x H.sub.2x).sub.m OH

in the desired ratio is used in place of R₁ OH. Alternatively, thecompounds of Formula III are heated together with less than 3-aequivalents of

    Z(OC.sub.x H.sub.2x).sub.m OH

under conditions such that R₁ OH is removed from the system.

The following compounds are illustrative of the compounds of FormulaVII:

    [H(OC.sub.2 H.sub.6).sub.6 O](C.sub.2 H.sub.5 O).sub.2 SiCHC.sub.12 H.sub.25 N.sup.+[(C.sub.2 H.sub.4 O).sub.10 H].sub.2 C.sub.6 H.sub.13 Br.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.3 O].sub.2 (C.sub.2 H.sub.5 O)SiCHCH.sub.3 N.sup.+[(C.sub.2 H.sub.4 O)C.sub.2 H.sub.5 ].sub.2 C.sub.6 H.sub.5 CH.sub.3  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.12 O](C.sub.4 H.sub.8 O).sub.2 SiCHC.sub.2 H.sub.5 N.sup.+[(C.sub.2 H.sub.4 O).sub.4 COCH.sub.3 ].sub.2 C.sub.10 H.sub.21 Cl.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4).sub.3 O](C.sub.2 H.sub.5) (CH.sub.3 O)SiCHCH.sub.3 N.sup.+(O).sup.-(CH.sub.3)C.sub.6 H.sub.13

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.14 O].sub.2 (C.sub.4 H.sub.9 O)SiCHC.sub.6 H.sub.13 N.sup.+(C.sub.6 H.sub.12 OH)(CH.sub.3)C.sub.5 H.sub.11  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.16 O].sub.2 (CH.sub.3 O)SiCHC.sub.4 H.sub.9 P.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.2 O].sub.2 (CH.sub.3 O)SiCHC.sub.10 H.sub.2] P.sup.+[ (C.sub.3 H.sub.7 O).sub.3 C.sub.2 H.sub.5 ] (C.sub.4 H.sub.9).sub.2  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.6 O](CH.sub.3 O).sub.2 SiCHCH.sub.3 P.sup.+(C.sub.3 H.sub.6 COOH).sub.2 CH.sub.3  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.10 O].sub.2 (C.sub.3 H.sub.7 O)SiCHC.sub.5 HH.sub.11 S.sup.+(CH.sub.3)C.sub.12 H.sub.25  Cl.sup.-

    [H(OC.sub.4 H.sub.8).sub.2 O].sub.2 (CH.sub.3 O)SiCHC.sub.8 H.sub.17 S.sup.+CH.sub.3 C.sub.6 H.sub.5  Br.sup.-

Commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt, U.S. Ser. No. 570,537, filed Apr. 22, 1975discloses the preparation of the compounds. (The disclosure of thisapplication is herein incorporated by reference.) ##STR12## wherein R₁is a C₁₋₄ alkyl group, a is 0-2, R₂ is a C₁₋₁₂ alkyl group, b is 1-3, R₄is a C₁₋₁₂ alkyl, aryl or arylalkyl group, a carboxy-substituted C₁₋₄alkyl group,

    (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group or aC₁₋₄ acyl group, or oxygen provided only one R₄ is oxygen, R₅ is a C₁₋₁₂alkyl, aryl or arylalkyl group, X is halide, Y is N, S or P and the sumof the carbon atoms in R₂, R₅ and R₄ when R₄ is alkyl, aryl, arylalkylor carboxy-substituted alkyl does not exceed 20.

The compounds of Formula VIII are prepared by initially reacting (when ais 0 and b is 3) trihalosilane with an alcohol (R₁ OH) at 0° to 50° C.for 1 to 10 hours to produce a trialkoxysilane. This silane is thenreacted with an allylglycidylether ##STR13## in the presence of 0.01 to0.1% chloroplatinic acid or platinum at 100° C. for 2 to 10 hours. Theresultant product ##STR14## is reacted with a tertiary amine, tertiaryphosphine, or dialkylsulfide in the presence of an acid in an inertsolvent at 60° to 100° C. for 1 to 10 hours to produce the ccompound ofFormula X. R₄ is an alkyl group, carboxy-substituted alkyl group, oxygenor a

    (C.sub.x H.sub.2x O).sub.m Z

group as defined above.

When a is 1 or 2, the preparation of the compounds is essentially theame except for the use of an alkyl substituted silane as the startingreactant.

When b is 2 in Formula VIII, a trihalovinylsilane of formula

    X.sub.3 SiCH=CH.sub.2

(which is commercially available) is reacted with hydrogen bromide inthe presence of peroxide or light to produce abeta-haloethyltrihalosilane. This compound is reacted with an alcohol,an allylglycidylether, and finally with an appropriate amine, phosphine,or sulfide in the manner discussed above for the preparation of thecompounds of Formula VIII when b is 3.

When b is 1 in Formula VIII, the starting reactant is a commerciallyavailable trihalometylsilane of formula

    X.sub.3 SiCH.sub.3

this silane is reacted with chlorine or, preferably a half mole ofbromine and a half mole of chlorine in the presence of light (such asprovided by an ordinary tungsten or fluorescent lamp). The resultantalpha-halomethyltrihalosilane is reacted with an alcohol, anallylglycidylether, and finally an appropriate amine, phosphine orsulfide in the manner discussed above with the compounds of Formula VIIIwhen b is 3.

The following compounds illustrate the compounds of Formula VIII.

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 N.sup.+ (CH.sub.3).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    (CH.sub.3 O).sub.2 C.sub.2 H.sub.5 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+ (C.sub.3 H.sub.6 COOH) (C.sub.4 H.sub.9)C.sub.8 H.sub.17  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(C.sub.2 H.sub.4 OH).sub.2 C.sub.6 H.sub.5  Br.sup.-

    (CH.sub.3 O).sub.3 Si(CH.sub.2 ).sub.3 OCH.sub.2 CHOHCH.sub.2 N.sup.+(O) (CH.sub.3)C.sub.8 H.sub.17

    (CH.sub.3 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O)H].sub.2 C.sub.10 H.sub.21  Br.sup.-

    (CH.sub.3 O).sub.2 C.sub.2 H.sub.5 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.3 H.sub.6 O).sub.12 C.sub.2 H.sub.5 ](CH.sub.3).sub.2 Cl.sup.-

    (C.sub.4 H.sub.9 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.3 COCH.sub.3].sub.2 CH.sub.3  Br.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(C.sub.4 H.sub.9).sub. 2 CH.sub.2 C.sub.6 H.sub.5  Br.sup.-

    (C.sub.4 H.sub.9 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(C.sub.2 H.sub.4 COOH).sub.2 C.sub.8.sub.17  Cl.sup.-

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(C.sub.2 H.sub.4 OH)(C.sub.2 H.sub.5)C.sub.10 H.sub.21  Cl.sup.-

    (CH.sub.3 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(O).sup.-(CH.sub.3)C.sub.10 H.sub.21

    (CH.sub.3 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+[C.sub.3 H.sub.6 O).sub.18 H].sub.2 CH.sub.3  Br.sup.-

    (C.sub.2 H.sub.5 O) (CH.sub.3).sub.2 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+[(C.sub.2 H.sub.4 O)CH.sub.3].sub.2 C.sub.6 H.sub.13

    (CH.sub.3 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(CH.sub.3)C.sub.6 H.sub.4 CH.sub.3  Cl.sup.-

    (CH.sub.3 O).sub.2 C.sub.7 H.sub.15 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(C.sub.2 H.sub.4 COOH)C.sub.8 H.sub.17  Cl.sup.-

    (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(C.sub.2 H.sub.4 OH)C.sub.6 H.sub.13  Cl.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(O).sup.-C.sub.10 H.sub.21

    (CH.sub.3 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.12 H]CH.sub.3  Br.sup.-

    (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.2 C.sub.3 H.sub.7 ]C.sub.2 H.sub.5 Br.sup.-

Commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt, U.S.. Ser. No. 570,537, filed Apr. 22, 1975discloses the preparation of these compounds. (The disclosure of thisapplication is herein incorporated by reference.) ##STR15## wherein Z ishydrogen, a C₁₋₃ alkyl group or a C₁₋₄ acyl group, x is 2-4, m is 1-20,a is 0-2, R₂ is a C₁₋₁₂ alkyl group, b is 1-3, R₄ is a C₁₋₁₂ alkyl, arylor arylalkyl group, a carboxy-substituted C₁₋₄ alkyl group

    (C.sub.x H.sub.2x O).sub.m Z

where x is 2-4, m is 1-20, and Z is hydrogen, a C₁₋₃ alkyl group or aC₁₋₄ acyl group, or oxygen provided only one R₄ is oxygen, R₅ ia a C₁₋₁₂alkyl, aryl or arylalkyl group, X is a halide, Y is N, S or P and thesum of the carbon atoms in R₂, R₅, and R₄ and R₄ is alkyl, aryl,arylalkyl or carboxy-substituted alkyl does not exceed 20.

compounds of Formula IX are prepared in a manner identical with that ofFormula VIII except that R₁ OH is replaced by

    HO(C.sub.x H.sub.2x O).sub.m Z.

the following compounds are exemplary of Formula IX compounds.

    [H(OC.sub.2 H.sub.4).sub.20 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.10 H.sub.21  Cl.sup.-

    [CH.sub.3 (OC.sub.3 H.sub.6).sub.10 O].sub.2 CH.sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(C.sub.2 H.sub.4 COOH) (C.sub.4 H.sub.9).sub.2 Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.2 O].sub.3 Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 N.sup.+(C.sub.2 H.sub.4 OH).sub.2 (C.sub.8 H.sub.17) Cl.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4)O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(O).sup.-(C.sub.4 H.sub.9)C.sub.6 H.sub.5

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.6 O].sub.3 Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.10 H].sub.2 CH.sub.3  Cl.sup.-

    [H(OC.sub.3 H.sub.6).sub.8 O].sub.2 C.sub.12 H.sub.25 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.8 C.sub.3 H.sub.7 ](CH.sub.3).sub.2  Br.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.4 O].sub.3 SiCH.sub.2 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.2 COCH.sub.3 ].sub.2 CH.sub.3  Br.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.3 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(C.sub.2 H.sub.5).sub.2 C.sub.8 H.sub.17  Cl.sup.-

    [H(OC.sub.3 H.sub.6).sub.8 ].sub.3 Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 P.sup.+(C.sub.3 H.sub.6 COOH).sub.2 C.sub.6 H.sub.13  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.2 O].sub.2 CH.sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(C.sub.2 H.sub.4 OH)(CH.sub.3)C.sub.8 H.sub.17  Cl.sup.-

    [CH.sub.3 (OC.sub.3 H.sub.6)O].sub.3 Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 P.sup.+(O).sup.-(CH.sub.3 )C.sub.10 H.sub.21

    [C.sub.2 H.sub.5 (OH.sub.4 C.sub.2).sub.12 O].sub.3 Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+[(C.sub.2 H.sub.4 O).sub.2 H].sub.2 C.sub.6 H.sub.4 CH.sub.3  Br.sup.-

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.8 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+[(C.sub.3 H.sub.6 O).sub.8 C.sub.2 H.sub.5 ](C.sub.4 H.sub.9).sub.2  Cl.sup.-

    [H(OC.sub.2 H).sub.4 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(CH.sub.3)C.sub.11 H.sub.23  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.6 O].sub.2 C.sub.4 H.sub.9 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(C.sub.3 H.sub.6 COOH)C.sub.10 H.sub.21  Cl.sup.-

    [CH.sub.3 (OC.sub.4 H.sub.8).sub.4 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(C.sub.4 H.sub.8 OH)C.sub.8 H.sub.17  Br.sup.-

    [H(OC.sub.2 H.sub.4).sub.14 O].sub.3 Si(CH).sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(O).sup.-C.sub.6 H.sub.12 C.sub.6 H.sub.5

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4)O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.6 H]C.sub.6 H.sub.13  Cl.sup.-

    [C.sub.2 H.sub.5 CO(OC.sub.2 H.sub.4).sub.2 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+[(C.sub.4 H.sub.8 O).sub.12 CH.sub.3 ]C.sub.8 H.sub.17  Cl.sup.-

Commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt U.S. Ser. No. 570,531, filed Apr. 22, 1975 disclosesthe preparation of these compounds. (The disclosure of this applicationis herein incorporated by reference). ##STR16## wherein Z is hydrogen, aC₁₋₃ alkyl group or a C₁₋₄ acyl group, x is 2-4, m is 1-20, R₂ is aC₁₋₁₂ alkyl group, R₁ is a C₁₋₄ alkyl group, a is 0 or 1, d is 1 or 2provided a+d does not exceed 2, b is 1-3, R₄ is a C₁₋₁₂ alkyl, aryl orarylalkyl group, a carboxy-substituted C₁₋₄ alkyl group,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen, R₅ is a C₁₋₁₂ alkyl, aryl or arylalkyl group, X is halide, Y isN, S or P and the sum of the carbon atoms in R₂, R₅ and R₄ when R₄ isalkyl, aryl, arylalkyl or carboxy-substituted alkyl does not exceed 20.

These compounds are prepared in a manner similar to that described forthe compounds of Example IX except that only a part of the R₁ OH isreplaced by

    HO(C.sub.x H.sub.2x O).sub.m Z.

the following compounds are examples of compounds having the formula X.

    [H(OC.sub.2 H.sub.4).sub.12 O](CH.sub.3 O).sub.2 SICH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25  Cl.sup.-

    [H(OC.sub.3 H.sub.6 O).sub.3 O](C.sub.2 H.sub.5 O)(CH.sub.3)Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(CH.sub.2 COOH)(C.sub.4 H.sub.9).sub.2  Cl.sup.-

    [C.sub.2 H.sub.5 (OC.sub.2 H.sub.4).sub.9 O](C.sub.2 H.sub.5 O).sub.2 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+(C.sub.6 H.sub.8 OH).sub.2 CH.sub.3  Cl.sup.-

    [CH.sub.3 (OC.sub.4 H.sub.8).sub.2 O].sub.2 (C.sub.4 H.sub.9 O)Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 N.sup.+(O).sup.-(CH.sub.3)C.sub.10 H.sub.21

    [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.6 O].sub.2 (CH.sub.3 O)SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.8 H].sub.2 CH.sub.3  Br.sup.-

    [H(OC.sub.2 H.sub.4).sub.18 O](C.sub.2 H.sub.5 O)(C.sub.10 H.sub.21)SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O)C.sub.3 H.sub.7](CH.sub.3).sub.2  Cl.sup.-

    [H(OC.sub.2 H.sub.4).sub.8 O](C.sub.2 H.sub.5 O).sub.2 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+(CH.sub.3).sub.2 C.sub.6 H.sub.5  Cl.sup.-

    [CH.sub.3 (OC.sub.2 H.sub.4).sub.6 O](C.sub.12 H.sub.25)(CH.sub.3 O)SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 P.sup.+[(C.sub.2 H.sub.4 O).sub.6 OCH.sub.3 ].sub.2 (CH.sub.3) Cl.sup.-

    [CH.sub.3 CO(OC.sub.3 H.sub.6).sub.4 O].sub.2 (CH.sub.3 O)Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 p.sup.+(C.sub.4 H.sub.8 OH).sub.2 CH.sub.3  Cl.sup.-

    [H(OC.sub.4 H.sub.8).sub.2 O](CH.sub.3 O)(CH.sub.3 O)(CH.sub.3)SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+[(C.sub.2 H.sub.4 O).sub.3 H]C.sub.2 H.sub.5  Cl.sup.-

    [C.sub.3 H.sub.7 (OC.sub.2 H.sub.4 O](C.sub.4 H.sub.9 O](C.sub.4 H.sub.9 O).sub.2 Si(CH.sub.2).sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(C.sub.3 H.sub.6 COOH)CH.sub.3  Br.sup.-

    [C.sub.2 H.sub.5 CO(OC.sub.2 H.sub.4).sub.10 O].sub.2 (C.sub.2 H.sub.5 O)SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2 S.sup.+(O).sup.-C.sub.12 H.sub.25

commonly assigned copending patent application "Organosilane Compounds"by Heckert and Watt U.S. Ser. No. 570,531, filed Apr. 22, 1975 disclosesthe preparation of these compounds. (The disclosure of this applicationis herein incorporated by reference.)

Siloxane oligomers of the above organosilanes are also useful in thepresent invention. Such oligomers are formed from the monomers by thecontrolled addition of from 1 to 100 equivalents of water, preferably inan inert solvent such as alcohol, tetrahydrofuran, etc. As used herein,"oligomers" is used to mean a degree of polymerization of from 2 to 100,preferably 2 to 20. A higher degree of polymerization adversely affectsthe ability of the compound to bond itself to the hard surface and isfor this reason avoided. Examples of siloxane oligomers having varyingdegrees of polymerization are readily visualized from the above examplesof organosilane monomers.

Water-soluble organic anionic detergents are used. U.S. Pat. No.3,579,454 issued May 18, 1971 to Everett J. Collier, Col. 11, line 49 toCol. 12, line 15 (the disclosure of which is herein incorporated byreference) describes suitable detergents which fall within theabove-described class. The ratio of organosilane to anionic detergent isfrom 1:1 to 1:10,000, preferably 1:1 to 1:500, most preferably 1:3 to1:60. An amount of organosilane below 1:10000 does not initially providea noticeable soil release benefit. A benefit is realized fromcompositions containing a ratio of organosilane to detergent of lessthan 1:10000 after repeated washings due to a gradual buildup ofdeposited organosilane, but is, for all practical purposes, too gradualto be of significance. The upper level of organosilane in thecomposition is dictated by cost and the fact that no noticeableadditional soil release benefit is obtained. Generally, the amount oforganosilane in a detergent composition does not exceed 10%.

When metallic or vitreous surfaces are contacted with a detergentcomposition containing the above-described organosilanes, a thin coatingof the organosilane is attached to the surfaces. It is theorized thatthe positively charged organosilane is attracted to negatively chargedmetallic or vitreous surface. The silicon atom in the organosilane formsa bond with the surface. The presence of the positive charge on theorganosilane is necessary to allow the bonding to take place within areasonable time when the organosilane is applied from a dilute systemsuch as is normally encountered in detergent composition uses. Theterminal alkyl groups attached to the positively charged compoundprovide the soil release benefits. It is believed that the organosilanecompound polymerizes on the surface to form a thin coating of thepolymer. The coating is responsible for imparting the soil releasebenefits to the surface. That is a hard surface having on it thepolymeric coating will be soiled; however, the soil is not tenaciouslybound to the surface by virtue of the coating and for this reason iseasily washed away.

Repeated washing will subsequently remove the polymeric coating.However, the soil release benefit is renewed by using the detergentcompositions of this invention. The ability to provide a soil releasebenefit from a wash or rinse solution is especially beneficial in thatit allows the consumer to efficiently and economically impart thebenefit to a hard surface without adversely affecting its appearance.

Detergent compositions in which the organosilane compound is includedare described in the following paragraphs.

Light Duty Liquid Detergent Composition

Detergent compositions intended for use in the hand washing of cookingutensils and table ware are generally formulated in a liquid form. Thecomposition consists essentially of from 0.01 to 10%, preferably 0.1 to2% of the organosilane; from 10 to 90%, preferably 20 to 40% of ananionic detergent as above described, and the balance water. Anelectrolyte such as potassium or sodium chloride is optionally includedat a level of from 0.5 to 5%, preferably 1 to 2%. A hydrotrope, e.g.toluene sulfonate, cumene sulfonate, or xylene sulfonate is optionallyincluded in the composition at a level of from 1 to 20%, preferably 2 to5%. An alcohol, e.g. a C₁₋₄ alcohol, may be a part of the composition ata level of from 1 to 2%, preferably 3 to 10%.

Window Cleaner

Window cleaner compositions contain from 0.001 to 5%, preferably 0.002to 1% of the organosilane. The remainder of the window cleanercomposition consists essentially of from 0.1 to 5%, preferably 0.5 to 3%of a water-soluble anionic detergent and the balance organic inertsolvent or solvent/water mixture. Suitable organic inert solventsinclude the following: methanol, ethanol, isopropanol, acetone, andmethyl ethyl ketone.

Car Wash Detergent Composition

A detergent composition intended for use in an automatic car washconsists essentially of from 0.01 to 10%, preferably 0.1 to 2% of theorganosilane; from 20 to 35%, preferably 23 to 28% of the anionicdetergent; and the balance water. Optionally from 1 to 10%, preferably 1to 3% of magnesium sulfate is included in the composition.

In Tank Toilet Bowl Cleaner

In tank toilet bowl cleaners consist essentially of from 0.01 to 10%,preferably 0.5 to 2% of the organosilane; from 0.5 to 20%, preferably 1to 15% of the anionic detergent; from 0.1 to 5%, preferably 0.5 to 2% ofsodium bisulfate; from 0.1 to 20%, preferably 1 to 15% of a loweralcohol, i.e., a C₁₋₄ alcohol; and the balance water.

Abrasive Cleaner

The organosilane of this invention can also be used in a detergentcomposition intended for the cleaning of hard surfaces such as ovens.Such compositions contain from 0.002 to 5%, preferably 0.01 to 1% of theorganosilane; from 0.1 to 10%, preferably 1 to 5% of a water-solubleanionic detergent; and from 50 to 95%, preferably 50 to 75% of awater-insoluble abrasive. Suitable abrasives include the following:quartz, pumice, pumicate, talc, silica sand, calcium carbonate, chinaclay, zirconium silicate, bentonite, diatomaceous earth, whiting,feldspar and aluminum oxide.

Nonionic, zwitterionic, and ampholytic detergents may be included in theabove-described compositions at low levels, e.g. not greater than 50%based on the total detergent level. Such minor additions do notmaterially affect the performance of the present compositions.

The following examples are illustrative of this invention.

EXAMPLE I

The organosilanes of this invention are tested for their ability toprovide a soil release benefit to hard surfaces in the manner describedimmediately below.

A solution of 0.003% organosilane and 0.06% sodium dodecyl sulfate indistilled water is prepared. The solution has a temperature of 55° C. Aclean glass slide is dipped into the solution and held there for 10minutes. The solution is continuously mixed while the glass slide isbeing treated. After the 10 minute hold time, the glass slide is removedand rinsed with tap water having a temperature of about 15° C. Therinsed slide is dried at 72° C. for 20 minutes.

Next the slide is soiled by dipping it into an oatmeal slurry for 15seconds and baking it for 20 minutes at 72° C. Thereafter, the slide iswashed with distilled water in a tergotometer for 3 minutes at 55° C.The resultant slide is dyed with a solution of iodide and potassiumiodide in water to facilitate its grading.

The slide is graded visually and assigned a number ranging from 0 (equalto an untreated glass slide, i.e., the control) to 4 (a totally cleanslide). Intermediate grades of 1 (slightly better than control), 2 (adefinite noticeable improvement) and 3 (slide is almost clean) are used.

Each organosilane is tested 5 times in the manner above described andits average is recorded. The individual organosilanes and their gradesare reported below.

    __________________________________________________________________________                                    Grade                                         __________________________________________________________________________    (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(O).sup.-(CH.sub.3)C.sub.12       H.sub.25                        4                                             (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 S.sup.+(O).sup.-C.sub.12 H.sub.25                                        4                                             (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).sub.2 C.sub.6         H.sub.4 C.sub.3 H.sub.7 Cl.sup.-                                                                              3                                             (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.4 OH)(CH.sub.3)C.sub.1    2 H.sub.25 Cl.sup.+             4                                             (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 OCH.sub.2 CHOHCH.sub.2 N.sup.+(CH.su    b.3).sub.2 C.sub.8 H.sub.17 Cl.sup.-                                                                          1.5                                           (C.sub.2 H.sub.5 O).sub.2 C.sub.4 H.sub.9 SiCH.sub.2 N.sup.+(CH.sub.3).sub    .2 C.sub.12 H.sub.25 Cl.sup.-   4                                             [H(OC.sub.2 H.sub.4).sub.18 O]].sub.3 SiCH.sub.2 N.sup.+(C.sub.2 H.sub.       5).sub.2 C.sub.10 H.sub.21 Cl.sup.-                                                                           4                                             [CH.sub.3 (OC.sub.2 H.sub.4).sub.12 O].sub.2 CH.sub.3 SiCH.sub.2 N.sup.+(C    H.sub.3).sub.2 C.sub.12 H.sub.25 Br.sup.-                                                                     4                                             [CH.sub.3 CO(OC.sub.2 H.sub.4).sub.4]3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3    ).sub.2 C.sub.10 H.sub.21 Cl.sup.-                                                                            4                                             [H(OC.sub.2 H.sub.4).sub.8] (CH.sub.3 O).sub.2 SiCH.sub.2 N.sup.+(CH.sub.3    ).sub.2 C.sub.12 H.sub.25 Cl.sup.-                                                                            4                                             [CH.sub.3 (OC.sub.2 H.sub.4).sub.6 O].sub.3 SiCH(C.sub.12 H.sub.25)N.sup.+    (CH.sub.3).sub.3 Br.sup.-       4                                             [H(OC.sub.2 H.sub.4).sub.2 O].sub.2 (CH.sub.3 O)SiCH(C.sub.8 H.sub.17)N.su    p.+(CH.sub.3).sub.2 C.sub.6 H.sub.13 Cl.sup.-                                                                 4                                             [H(OC.sub.2 H.sub.4).sub.4 O].sub.3 SiCH.sub.2 OCH.sub.2 CHOHCH.sub.2         N.sup.+(CH.sub.3).sub.2 C.sub.12 H.sub.25 Cl.sup.-                                                            3                                             [CH.sub.3 (OC.sub.2 H.sub.4).sub.8 O].sub.2 (CH.sub.3 O)SiCH.sub.2            OCH.sub.2 CHOHCH.sub.2 N.sup.+(C.sub.4 H.sub.9).sub.3 Cl.sup.-2               (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.12         H.sub.25 Cl.sup.-               4                                             (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 P.sup.+(CH.sub.3).sub.2 C.sub.12         H.sub.25 Cl.sup.-               4                                             (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.2 N.sup.+(CH.sub.3).sub.2          C.sub.12 H.sub.25 Cl.sup.-      4                                             (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).sub.2          C.sub.12 H.sub.25 Br.sup.-      4                                             (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.6          H.sub.13 Cl.sup.-               1                                             (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.6 H.sub.5         Cl.sup.-                        1                                             (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.8          H.sub.17 Cl.sup.-               4                                             (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 S.sup.+(CH.sub.3)C.sub.10 H.sub.21       Cl.sup.-                        4                                             (C.sub.4 H.sub.8 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.2          H.sub.4 C.sub.6 H.sub.5 Cl.sup.-                                                                              4                                             (CH.sub.3 O).sub.3 SiCH.sub.2 N.sup.+[(C.sub.3 H.sub.6 O).sub.3 C.sub.2       H.sub.5]2 C.sub.8 H.sub.17 Cl.sup.-                                                                           1                                             (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(C.sub.2 H.sub.5)[(C.s    ub.4 H.sub.9 O).sub.8 H]C.sub.4 H.sub.9 Cl.sup.-                                                              1.5                                           (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(C.sub.3 H.sub.7 COOH).sub.2      C.sub.8 H.sub.17 Cl.sup.-       1                                             (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+[(C.sub.2 H.sub.4 O).sub.4        COCH.sub.3]2 C.sub.8 H.sub.17 Cl.sup.-                                                                        2.5                                           (C.sub.2 H.sub.5 O).sub.3 SiCH(C.sub.12 H.sub.25)N.sup.+(C.sub.2 H.sub.5).    sub.3 Cl.sup.-                  4                                             (C.sub.2 H.sub.5 O).sub.3 SiCH(C.sub.12 H.sub.25 P.sup.+(C.sub.2 H.sub.5).    sub.3 Cl.sup.-                  4                                             (CH.sub.3 O).sub.2 CH.sub.3 SiCH(C.sub.8 H.sub.17)N.sup.+(CH.sub.3).sub.3     Br.sup.-                        4                                             (CH.sub.3 O).sub.2 CH.sub.3 SiCH(C.sub.10 H.sub.21)S.sup.+(CH.sub.3).sub.2     Br.sup.-                       4                                             Siloxane dimer of (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).s    ub.2 C.sub.12 H.sub.25 Cl.sup.- 4                                             Siloxane dimer of (C.sub.2 H.sub.5 O).sub.2 (CH.sub.3)SiCH.sub.2 N.sup.+(C    H.sub.3).sub.2 C.sub.8 H.sub.17 Cl.sup.-                                                                      3                                             Siloxane trimer of (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 P.sup.+(CH.sub.3)    .sub.2 C.sub.12 H.sub.25 Cl.sup.-                                                                             4                                             Siloxane dimer of (CH.sub.3 O).sub.3 SiCH.sub.2 S.sup.+(CH.sub.3)C.sub.12     H.sub.25 Cl.sup.-               4                                             __________________________________________________________________________

Different anionic detergents mixed with the above organosilanes in anorganosilane to anionic detergent ratio of 1:1 to 1:10,000 givesubstantially the same grades. An absence of any turbidity after 20 daysat 20° C. indicates that the the components are compatible.

The following are examples of detergent compositions which contain theorganosilane of this invention and which impart a noticeable soilrelease benefit to metallic and vitreous surfaces contacted therewith.

EXAMPLE II

                  EXAMPLE II                                                      ______________________________________                                        Light Duty Liquid Detergent Composition                                       ______________________________________                                        Sodium salt of sulfated                                                                            23.0%                                                    coconut alcohol                                                               (C.sub.2 H.sub.5 O).sub.3 SiCH.sub.2 N.sup.+(CH.sub.3).sub.2 C.sub.8          H.sub.17 Cl.sup.-     1.0%                                                    Water                76.0%                                                    ______________________________________                                    

When (C₂ H₅ O)₃ SiCH₂ P⁺(CH₃)₂ C₈ H₁₇ Cl⁻ or (C₂ H₅ O)₃ SiCH₂ S⁺(CH₃)C₈H₁₇ Cl⁻ is substituted for the organosilane of Example II, substantiallythe same results are obtained.

EXAMPLE III

                  EXAMPLE III                                                     ______________________________________                                        Light Duty Liquid Detergent Composition                                       ______________________________________                                        Sodium salt of sulfated coconut                                                                        22.8%                                                 alcohol ethoxylated with 3 moles                                              of ethylene oxide                                                            Sodium salt of sulfated coconut alcohol                                                                4.5%                                                 (CH.sub.3 O).sub.2 C.sub.10 H.sub.21 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).    sub.3 Cl.sup.-           0.05%                                                Potassium chloride       2.0%                                                 Dimethyldodecylamine oxide                                                                             5.0%                                                 Ethanol                  6.0%                                                 Water                    balance                                              ______________________________________                                    

EXAMPLE IV

                  EXAMPLE IV                                                      ______________________________________                                        Abrasive Cleaner                                                              ______________________________________                                        Sodium linear C.sub.12 alkyl benzene                                                                   5.0%                                                  sulfonate                                                                    (CH.sub.3 O).sub.2 C.sub.2 H.sub.5 Si(CH.sub.2).sub.3 N.sup.+(C.sub.2         H.sub.5).sub.2 C.sub.8 H.sub.17 Cl.sup.-                                                               0.5%                                                 Silica                   90.0%                                                Misc. (water, perfume, dye, etc.)                                                                      balance                                              ______________________________________                                    

Substantially the same results are obtained when (CH₃ O)₂ C₂ H₅ Si(CH₂)₃P⁺(C₂ H₅)₂ C₈ H₁₇ Cl⁻ or (CH₃ O)₂ C₂ H₅ Si(CH₂)₃ S⁺(C₂ H₅)C₈ H₁₇ Cl⁻ issubstituted for the organosilane of Example IV.

EXAMPLE V

                  EXAMPLE V                                                       ______________________________________                                        Car Wash Detergent Composition                                                ______________________________________                                        Sodium salt of sulfated coconut                                                                        26.0%                                                 alcohol ethoxylated with 3 moles                                              of ethylene oxide                                                            (CH.sub.3 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).sub.2 CH.sub.2        C.sub.6 H.sub.5 Cl.sup.- 1.5%                                                 Magnesium sulfate        1.5%                                                 Water                    balance                                              ______________________________________                                    

The use of (CH₃ O)₃ Si(CH₂)₃ P⁺(CH₃)₂ CH₂ C₆ H₅ Cl⁻ or (CH₃ O)₃ Si(CH₂)₃S⁺(CH₃)CH₂ C₆ H₅ Cl⁻ in this example gives substantially the sameresults.

EXAMPLE IV

                  EXAMPLE VI                                                      ______________________________________                                        Window Cleaner                                                                ______________________________________                                        Sodium C.sub.14  alkyl sulfate                                                                         3.0%                                                 (C.sub.2 H.sub.5 O).sub.3 Si(CH.sub.2).sub.3 N.sup.+(CH.sub.3).sub.2          C.sub.8 H.sub.17 Br.sup.-                                                                              .05%                                                 Isopropanol              96.95%                                               ______________________________________                                    

When (C₂ H₅ O)₃ Si(CH₂)₃ P⁺(CH₃)₂ C₈ H₁₇ Br⁻ or (C₂ H₅ O)₃ Si(CH₂)₃S⁺(CH₃)C₈ H₁₇ Br⁻ is substituted for the organosilane of Example VIsubstantially the same results are obtained.

Replacement of the organosilanes of Examples II-VI with theorganosilanes of Example I gives satisfactory products in that anoticeable soil release benefit is obtained.

The composition of this invention are generally diluted with waterduring usage. Under normal usage conditions, from 0.2 to 20 ppm oforganosilane is found in the wash or rinse solution. Surprisingly, evenfrom such a low concentration the organosilane molecule of thisinvention deposits itself upon hard surfaces in an amount sufficient toprovide a noticeable soil release benefit. As previously discussed, itis believed the positively charged atom in the molecule is largelyresponsible for the necessary deposition taking place under diluteconditions.

What is claimed is:
 1. A detergent composition capable of imparting soilrelease benefits to metallic and vitreous surfaces contacted therewithconsisting essentially of:a. an organosilane having the formula##STR17##or is a siloxane oligomer thereof wherein R₁ is an alkyl groupcontaining 1 to 4 carbon atoms, or

    Z(OCH.sub.x H.sub.2x).sub.m

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbons or an acyl group containing 1 to 4 carbonatoms; R₂ is an alkyl group containing 1 to 12 carbon atoms, a is 0 to2; R₃ is hydrogen or an alkyl group containing 1 to 12 carbon atoms, bis 1 to 3; c is 0 or 1; R₄ is an alkyl, aryl or arylalkyl groupcontaining 1 to 12 carbon atoms, a carboxy-substituted alkyl groupcontaining 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that there is no X⁻ when R₄ is oxygen; R₅ isan alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; X ishalide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₃, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed 20 carbon atoms; and b. awater-soluble organic anionic detergent in a weight ratio ororganosilane to detergent of from 1:1 to 1:10,000.
 2. The composition ofclaim 1 wherein the organosilane has the formula ##STR18##or is asiloxane oligomer thereof wherein Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, x is 2 to 4, and m is 1 to 20; R₂ is an alkyl group containing 1to 12 carbon atoms; a is 0 to 2; b is 1 to 3; R₄ is an alkyl, aryl orarylalkyl group containing 1 to 12 carbon atoms, a carboxy-substitutedalkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided than when R₄ is oxygen there is no X^(-;) R₅is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; Xis halide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed
 20. 3. The composition ofclaim 1 wherein the organosilane has the formula ##STR19##or is asiloxane oligomer thereof wherein Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, x is 2 to 4, and m is 1 to 20; R₂ is an alkyl group containing 1to 12 carbon atoms; R₁ is an alkyl group containing 1 to 4 carbon atoms,a is 0 to 1; d is 1 or 2 provided a+d does not exceed 2; b is 1 to 3; R₄is an alkyl, aryl or arylalkyl group containing 1 to 12 atoms, acarboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that when R₄ is oxygen there is no X^(-;) R₅is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; Xis halide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed
 20. 4. The composition ofclaim 1 wherein the organosilane has the formula ##STR20##or is asiloxane oligomer thereof wherein Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, x is 2 to 4, and m is 1 to 20; R₂ is an alkyl group containing 1to 18 carbon atoms; a is 0 to 2; R₃ is an alkyl group containing 1 to 12carbon atoms; R₄ is an alkyl, aryl or arylalkyl group containing 1 to 12carbon atoms, a carboxy-substituted alkyl group containing 1 to 4 carbonatoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that when R₄ is oxygen there is no X^(-;) R₅is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; Xis halide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₃, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed
 20. 5. The composition ofclaim 1 wherein the organosilane has the formula ##STR21##or is asiloxane oilgomer thereof wherein Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, x is 2 to 4, and m is 1 to 20; R₂ is an alkyl group containing 1to 3 carbon atoms; R₁ is an alky group containing 1 to 4 carbon atoms; ais 0 or 1; d is 1 or 2 provided a+d does not exceed 2; R₃ is an alkylgroup containing 1 to 12 carbon atoms; R₄ is an alkyl, aryl or arylalkylgroup containing 1 to 12 carbon atoms, a carboxy-substituted alkyl groupcontaining 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that when R₄ is oxygen there is no X^(-;) R₅is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; Xis halide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₃, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed
 20. 6. The composition ofclaim 1 wherein the organosilane has the formula ##STR22##or is asiloxane oligomer thereof wherein Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, x is 2 to 4, and m is 1 to 20; R₂ is an alkyl group containing 1to 12 carbon atoms; a is 0 to 2; b is 1 to 3; R₄ is an alkyl, aryl orarylalkyl group containing 1 to 12 carbon atoms, a carboxy-substitutedalkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that when R₄ is oxygen there is no X^(-;) R₅is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; Xis halide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl, orcarboxy-substituted alkyl does not exceed
 20. 7. The composition ofclaim 1 wherein the organosilane has the formula ##STR23## or is asiloxane oligomer thereof wherein Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, x is 2 to 4, and m is 1 to 20; R₂ is an alkyl group containing 1to 12 carbon atoms; R₁ is an alkyl group containing 1 to 4 carbon atoms;a is 0 or 1; d is 1 or 2 provided a+d does not exceed 2; b is 1 to 3; R₄is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, acarboxy-substituted alky group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that when R₄ is oxygen there is no X^(-;) R₅is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; Xis halide; and Y is nitrogen, sulfur or phosphorus and the sum of thecarbon atoms in R₂, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl orcarboxy-substituted alkyl does not exceed
 20. 8. The composition ofclaim 1 in which said organosilane has the formula ##STR24##or is asiloxane oligomer thereof wherein R₁ is an alkyl group containing 1 to 4carbon atoms, or

    Z(OC.sub.x H.sub.2x).sub.m

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbons or an acyl group containing 1 to 4 carbonatoms; R₂ is an alkyl group containing 1 to 12 carbon atoms; a is 0 to2; R₃ is hydrogen or an alkyl group containing 1 to 12 carbons atoms; bis 1 to 3; c is 0 or 1; R₄ is an alkyl, aryl or arylalkyl groupcontaining 1 to 12 carbon atoms, a carboxy-substituted alkyl groupcontaining 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x, m and Z are as defined above, or oxygen provided only one R₄ isoxygen and further provided that when R₄ is oxygen there is no X^(-;) R₅is alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms; and Xis halide; and the sum of the carbon atoms in R₂, R₃, R₅ and R₄ when R₄is alkly, aryl, arylalkyl or carboxy-substituted alkyl does not exceed20 carbon atoms.
 9. The composition of claim 1 wherein the organosilanehas the formula ##STR25##or is a siloxane oligomer thereof wherein R₁ isan alkyl group containing 1 to 4 carbon atoms; b is 1 to 3; R₄ is analkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms, acarboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 18 carbon atoms or an acyl group containing 1 to 4carbon atoms, or oxygen provided only one R₄ is oxygen and furtherprovided that when R₄ is oxygen there is no X^(-;) R₅ is an alkyl, arylor arylalkyl group containing 4 to 12 carbon atoms; X is a halide; and Yis nitrogen, sulfur or phosphorus and the sum of the carbon atoms in R₅and R₄, when R₄ is alkyl, aryl, aryl alkyl or carboxy-substituted alkyldoes not exceed
 20. 10. The composition of claim 1 wherein theorganosilane has the formula ##STR26##or is a siloxane oligomer thereofwherein R₁ is an alkyl group containing 1 to 4 carbon atoms; R₂ is analkyl group containing 1 to 12 carbon atoms; a is 1 or 2; b is 1 to 3;R₄ is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms,a carboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, or oxygen provided only one R₄ is oxygen and further providedthat when R₄ is oxygen there is no X^(-;) R₅ is an alkyl, aryl orarylalkyl group containing 1 to 12 carbon atoms; X is a halide; and Y isnitrogen, sulfur or phosphorus and the sum of the carbon atoms in R₂, R₅and R₄ when R₄ is alkyl, aryl, arylalkyl or carboxy-substituted alkyldoes not exceed
 20. 11. The composition of claim 1 wherein theorganosilane has the formula ##STR27##or is a siloxane oligomer thereofwherein R₁ is an alkyl group containing 1 to 4 carbon atoms; R₂ is analkyl group containing 1 to 12 carbon atoms; a is 0 to 2; R₃ is an alkylgroup containing 1 to 12 carbon atoms; R₄ is an alkyl, aryl or arylalkylgroup containing 1 to 12 carbon atoms, a carboxy-substituted alkyl groupcontaining 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, or oxygen provided only one R₄ is oxygen and further providedthat when R₄ is oxygen there is no X^(-;) R₅ is an alkyl, aryl orarylalkyl group containing 1 to 22 carbon atoms; X is a halide; and Y isnitrogen, sulfur or phosphorus and the sum of the carbon atoms in R₂,R₃, R₅ and R₄ when R₄ is alkyl, aryl, arylalkyl or carboxy-substitutedalkyl does not exceed
 20. 12. The composition of claim 1 wherein theorganosilane has the formula ##STR28##or is a siloxane oligomer thereofwherein R₁ is an alkyl group containing 1 to 4 carbon atoms; R₂ is analkyl group containing 1 to 12 carbon atoms; a is 0 to 2; b is 1 to 3;R₄ is an alkyl, aryl or arylalkyl group containing 1 to 12 carbon atoms,a carboxy-substituted alkyl group containing 1 to 4 carbon atoms,

    (C.sub.x H.sub.2x O).sub.m Z

where x is 2 to 4, m is 1 to 20, and Z is hydrogen, an alkyl groupcontaining 1 to 3 carbon atoms or an acyl group containing 1 to 4 carbonatoms, or oxygen provided only one R₄ is oxygen and further providedthat when R₄ is oxygen there is no X^(-;) R₅ is an alkyl, aryl orarylalkyl group containing 1 to 12 carbon atoms; X is a halide; and Y isnitrogen, sulfur or phosphorus and the sum of the carbon atoms in R₂, R₅and R₄ when R₄ is alkyl, aryl, arylalkyl or carboxy-substituted alkyldoes not exceed
 20. 13. The composition of claim 1 wherein b is 1, X ischloride or bromide and the sum of the carbon atoms in R₂, R₃, R₅, andR₄ when R₄ is alkyl, aryl, arylalkyl or carboxy-substituted alkyl doesnot exceed
 15. 14. The composition of claim 13 wherein the ratio oforganosilane to detergent is from 1:1 to 1:500.
 15. The composition ofclaim 1 intended for use as a window cleaner consisting essentiallyof:a. from 0.001 to 5% of the organosilane; b. from 0.1 to 5% of thewater-soluble organic anionic detergent; and c. the balance an inertorganic solvent.
 16. The composition of claim 1 intended for use as anabrasive cleaner consisting essentially of:a. from 0.002 to 5% of theorganosilane; b. from 0.1 to 10% of the water-soluble organic anionicdetergent; and c. from 50 to 95% of a water-soluble abrasive.
 17. Thecomposition of claim 1 intended for use as a car wash detergentcomposition consisting essentially of:a. from 0.01 to 10% of theorganosilane; b. from 20 to 35% of the water-soluble organic anionicdetergent; and d. the balance water.
 18. The composition of claim 1intended for use as in tank toilet bowl cleaner consisting essentiallyof:a. from 0.01 to 10% of the organosilane; b. from 0.5 to 20% of thewater-soluble organic anionic detergent; c. from 0.1 to 5% of sodiumbisulfate; d. from 0.1 to 20% of a lower alcohol; and d. the balancewater.
 19. The detergent composition of claim 1 wherein the organosilanehas the formula ##STR29##20.
 20. The composition of claim 1 intended foruse as a light-duty dishwashing composition consisting essentially of:a.from 0.01 to 10% of the organosilane; b. from 10 to 90% of thewater-soluble organic anionic detergent; and c. the balance water. 21.The composition of claim 20 consisting essentially of:a. from 0.1 to 2%of the organosilane b. from 20 to 40% of the water-soluble organicanionic detergent; and c. the balance water.
 22. The composition ofclaim 15 consisting essentially of:a. from 0.002 to 1% of theorganosilane; b. from 0.5 to 3% of the water-soluble organic anionicdetergent; and c. the balance the inert organic solvent.
 23. Thecomposition of claim 16 consisting essentially of:a. from 0.01 to 1% ofthe oganosilane; b. from 1 to 5% of the water-soluble organic anionicdetergent; and c. from 50 to 75% of the water-soluble abrasive.
 24. Thecomposition of claim 17 additionally containing from 1 to 10% ofmagnesium sulfate.
 25. The composition of claim 21 additionallycontaining from 0.5 to 5% of an electrolyte.
 26. The composition ofclaim 25 additionally containing from 1 to 20% of a hydrotrope and from1 to 20% of a lower alcohol.